Henry III's reign over Anglia is regarded by many as a failure largely due to his seeming inability to fulfill any of the essential tasks of a medieval monarch; rule wisely, wage war successfully and maintain the dynasty.

The eldest son of Charles IV and Philippa of Wessex, Henry was born in 1374 and was raised in the household of his aging grandfather, and namesake, Henry II. The young prince was very much the apple of his grandfather's eye and while the reins of government had largely been handed to the Witenage the king threw himself into Henry's education and development. Some of his earliest tutors were Henry II's great ministers while it would be the king's private channels which arranged his marriage to Catherine of Aquitaine. By the time he was in his teens he could speak Anglian, Latin, Greek, Low and High German, French and Danish. He is usually recognised as Anglia's best-educated ruler, at least until Anna II.

His marriage to Catherine of Aquitaine was fraught and apparently he cared little for her. Reports suggest he was greatly affected by his grandfather's death in 1390 and this seems to have instilled a sexual piety in him which the entreaties of the Witenage and his advisors could do little to shift. They kept separate courts and it known that Catherine petitioned her father and brother to help annul the marriage on more than one occasion. It was of great concern to the nobles that by the time of his father's death in 1423 the couple had been married for the best part of 15 years but had no children to show for it.

Neither had he shown any aptitude for war. He had been at the forefront of the renewed hostilities against France but often overruled the other lords who advocated a much more aggressive approach and instead the Anglian army engaged in a side-show of besieging castles. Increasingly excuses were made to keep him away from the army. This followed him into his reign and it is said his lords laughed behind his back whenever the topic of war-records ever came up. The general impression seems to have been of a bookish, and prudish man easily overawed by his more dynamic nobles. As a reaction to this he attempted to cultivate an air of 'majesty'. Whereas some European monarchies (like Bohemia, whose court he actively aped) had embraced the idea of divine right, Anglia's monarchy had so far maintained a more egalitarian view; the king was only the highest of the nobles and, moreover, the Witenage had right of election. Attempts to change this position only stirred up ill-will.

Much of his reign was made up of an ever-increasingly tense relationship with the Witenage, not only over his increasingly high-handed behaviour but more generally over money. Like his father before him Henry claimed the French throne, recognised by the Emperors Charles II and Sigismund I, but needed the men and money to advance the claim. His own personal spending had generally gotten out of control; the pageantry he put on in Flanders to try and curry the favour of potential allies in a war against France (and perhaps make up for the lack of previous glory on the battlefield) was a considerable drain, as was the never ending donations he handed out to the church, again for little discernible reward. While the Witenage refused to grant him extra taxes Henry III withdrew his justice and there was a notable breakdown in law and order. This was much blamed on soldiers, both Anglian and Flemish, returning from the French war without pay.

The grievances against his rule grew louder once the king had refused to endorse any law or judgment passed by the Witenage. Exhausted and the 'commons' appealed to sympathetic lords and in December 1436 an army was raised to bring 'the King back to his senses'. Captured him at his winter lodgings in Lincoln he was brought to the royal castle at Rockingham and asked to restore law to the kingdom. Initially refusing to allow the commons to dictate terms to him he hoped an army would rise to rescue him. However most lords were unwilling to instigate a civil war, and so instead backed the pleas of his brothers Richard of Kesteven and William of Hainault, plus his brother-in-law Matthew of Luxembourg on behalf of the Emperor Sigismund, would eventually change his mind. Reaffirming various charters Henry was released from confinement but descending the castle stairs he was seen, by a considerable crowd, to stumble and fall, breaking his neck. Though all involved swore an oath that it was an accident the inevitable rumour of murder was almost impossible to dispel. In a rather muted ceremony in Jorvik on Christmas Day his would-be rescuer Richard was crowned. Catherine of Aquitaine was quickly remarried to the widowed Earl of Essex, Sigurd Henriksson and they would have two children.

Considering his own education had been almost the finest available at the time it is fitting that Henry's one lasting achievement was the foundation of several colleges such as Kings' College in Lincoln, St Edmund's in Dunholm and St Ghislain in Mons.